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Condos and beach rentals in Kailua, HI

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All 111 Rentals in Kailua
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From
$95
Per Night
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1 / 11
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1 Bedroom, 1 Bathroom, Sleeps 4
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$126
Per Night
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1 / 16
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1 Bedroom, 1 Bathroom, Sleeps 2
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$395
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1 / 16
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3 Bedrooms, 3 Bathrooms, Sleeps 7
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$695
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1 / 26
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3 Bedrooms, 4 Bathrooms, Sleeps 8
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Amenities & Details
  • Dryer
  • Dishwasher
  • Deck
  • Refrigerator
  • Microwave
  • Ceiling Fans
  • Stove
  • DVD Player
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
This gorgeous, beautifully furnished Ocean View home is a stone's throw from Kailua Beach and sleeps up to 8 comfortably. There is a large, sparkling, fully tiled swimming pool, 2 jacuzzi tubs, central air conditioning, 3 large bedrooms with ocean views, and 4 baths. Dolphin Manor is an... View all property information
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5 of 5 stars Reviewed August 25, 2014
This is a lovely and comfortable home, just steps from Kailua Beach, that will give any traveler a wonderful taste of Hawaii. We walked the beach every morning, spent time in the...
5 of 5 stars Reviewed July 7, 2014
We rented the house for a family vacation and to attend our son's wedding wedding. It was everything we could of wanted. No surprises and in excellent condition. Great location...
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From
$265
Per Night
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1 / 13
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2 Bedrooms, 2 Bathrooms, Sleeps 4
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Amenities & Details
  • Fax
  • TV
  • Washer
  • Hot Tub
  • Stereo System
  • Ceiling Fans
  • Dryer
  • Microwave
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • x
About this property
Charming and Newly remodeled 2 Bedroom, 2 Bath Villa on private Beachside Estate with swimming pool and jacuzii. Just a short 2 minute walk to Kailua Beach through the park. Sleeps 4. View all property information
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3 of 5 stars Reviewed February 18, 2015
There are three separate rental residences on this property, and we rented all of them so that our family (daughter, her husband and two children, as well as our two adult sons...
4 of 5 stars Reviewed December 11, 2014
This was a great little find for our friends retreat. The only drawback was we had to walk through one bedroom to get to the other. Seeings as we were all friends it wasn't an...
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From
$1,200
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1 / 27
4 Bedrooms, 4 Bathrooms, Sleeps 10
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Amenities & Details
  • Stereo System
  • Satellite TV
  • Dryer
  • Washer
  • Dishwasher
  • TV
  • Ceiling Fans
  • DVD Player
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Maluhia is located just steps away from the white sandy shores of Kailua Beach. The small town of Kailua is busting with popular restaurants and boutiques, and just a short 5 minute drive or 15 minute bike ride away. Kailua is home to world famous Lanikai Beach. The two Mokulua islands are... View all property information
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From
$150
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1 / 15
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1 Bedroom, 1 Bathroom, Sleeps 2
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  • # Of Bathrooms
  • Guest Count
  • Number Of Bedrooms
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • x
  • Smoking allowed
  • Elder access
  • x
  • x
About this property
If you're looking for a perfect spot to call home during your stay in Kailua, you'll love this one bedroom/one bath apartment in walking distance of world-famous Kailua and Lanikai Beaches. This unit, which has just been made available as a monthly vacation rental, is tucked away in a quiet,... View all property information
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From
$290
Per Night
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1 / 10
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3 Bedrooms, 1 Bathroom, Sleeps 6
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Amenities & Details
  • Guest Count
  • # Of Bathrooms
  • Number Of Bedrooms
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
Aloha and welcome to this comfortable three bedroom one bath house. There is a large back deck with a hot tub. This vacation home sleeps 6 - 7, it has one new Sealy Posturepedic queen size bed, one new Sealy Posturepedic king and two twin size beds, with a sleeper sofa in the living room. This... View all property information
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From
$1,300
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1 / 24
5 Bedrooms, 4 Bathrooms, Sleeps 14
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Amenities & Details
  • Microwave
  • Patio
  • Refrigerator
  • Parking
  • Washer
  • Grill
  • Dryer
  • DVD Player
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Welcome to the world of John Walker. A Scotsman who made his way to Hawaii as a young man in the 1870's to become a contractor of choice to Queen Liliuokalani, and erect such notable buildings as the Bishop Museum and Honolulu Hale (City Hall). Mr. Walker's inviting presence is felt in the... View all property information
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$125
Per Night
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1 / 23
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1 Bedroom, 1 Bathroom, Sleeps 4
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Amenities & Details
  • Highchair
  • Parking
  • Microwave
  • Refrigerator
  • Wi-Fi
  • Dryer
  • Air Conditioning
  • Grill
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • Smoking allowed
  • Elder access
  • ?
  • ?
About this property
We have 2 properties located directly across the street from one another with two 1 bedroom/ 1 bathroom units between the two properties as well as a two spacious studios & 4 private rooms. All our units have their own private entrances and outside sitting areas. Both these properties are centrally... View all property information
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5 of 5 stars Reviewed February 13, 2015
We wanted to avoid the big city feel and crowds of Honolulu so we looked in Kailua. It was perfect. We were minutes from the sites in Honolulu but on the most beautiful beach on...
5 of 5 stars Reviewed October 29, 2014
I really enjoyed my stay here. The location was close to everything. The room was spacious and clean. The bed was super comfortable. The deal was amazing. I certainly would book...
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From
$325
Per Night
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1 / 22
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7 Bedrooms, 2 Bathrooms, Sleeps 8
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Amenities & Details
  • Dryer
  • Ceiling Fans
  • Refrigerator
  • Wi-Fi
  • Stove
  • Grill
  • Air Conditioning
  • Microwave
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • Smoking allowed
  • Elder access
  • ?
  • ?
About this property
A short peaceful 5 minute walk to the stunningly beautiful Kailua Beach will leave you in a state of bliss. Indulge yourself in an array of beach activities including swimming, snorkeling, kayaking, windsurfing and sunbathing as the tropical trade-winds pass by taking your worries with them.... View all property information
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5 of 5 stars Reviewed February 11, 2015
We were able to find this awesome accommodation last minute. The house is clean, spacious and in such a wonderful location. We were close to shopping, restaurants and the most...
3 of 5 stars Reviewed December 31, 2014
Average house, best thing is the location, but burners do not work. Just rather old fixtures. But all in all it was a nice stay.
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From
$115
Per Night
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1 / 15
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1 Bedroom, 1 Bathroom, Sleeps 3
Booking
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Amenities & Details
  • Dryer
  • Grill
  • Air Conditioning
  • Washer
  • Refrigerator
  • Microwave
  • TV
  • Ceiling Fans
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • Smoking allowed
  • Elder access
  • ?
  • ?
About this property
Lets be honest... one of the main reasons you're visiting Hawaii is for the beautiful weather year round and the jaw dropping beaches. Our vacation rentals are all within walking distance to one of the worlds most beautiful beaches, Kailua beach. Two of our properties (our Awakea & Ali'i... View all property information
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From
$150
Per Night
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1 / 18
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1 Bedroom, 1 Bathroom, Sleeps 3
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Amenities & Details
  • Grill
  • Patio
  • Satellite TV
  • VCR
  • Microwave
  • TV
  • Wi-Fi
  • Stove
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
A private 400 sq foot studio w/fenced courtyard/lanai, in quiet Kaimalino. Relax outdoors or indoors w/full kitchen, bath, cable and internet connections. A short walk will take you to a turtle nesting grounds, the open ocean facing Maui and Lanai islands, sandy Kailua Beach, and Aikahi Shopping... View all property information
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5 of 5 stars Reviewed December 31, 2014
We are so pleased with this cottage. The location was perfect for us and Usha was very hospitable. Kailua's beaches are seriously some of the most beautiful and quiet. Plenty of...
4 of 5 stars Reviewed August 13, 2014
This studio was exactly as advertised and more. It was an easy walk to a beautiful sunrise, supermarkets and restaurants but out of the way enough to avoid the traffic and noise...
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From
$399
Per Night
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1 / 16
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3 Bedrooms, 2 Bathrooms, Sleeps 10
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Amenities & Details
  • Dryer
  • Microwave
  • Patio
  • Parking
  • Ceiling Fans
  • Satellite TV
  • Grill
  • Refrigerator
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
Experience Hawaii at it's fullest by staying at this amazing 1926 bungalow located between two of the most beautiful beaches in the world. Lanikai and Kailua beaches are just 200 yards away. Kayak, Bicycle, Surfboard, Paddle board and Snorkel Rentals are 200 yards away at Kailua Beach Park. A... View all property information
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5 of 5 stars Reviewed July 18, 2014
We had two families totaling 4 adults and 5 kids stay at this house, and had a fabulous time! The house is beautiful, and set right between two lovely beaches. The house is not...
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From
$750
Per Night
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1 / 28
6 Bedrooms, 6 Bathrooms, Sleeps 14
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Amenities & Details
  • Ceiling Fans
  • DVD Player
  • Linens Provided
  • Air Conditioning
  • Stereo System
  • Satellite TV
  • Deck
  • Refrigerator
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
With access to the world-famous Kailua Beach and its turquoise waters being just four houses away and shops, restaurants and grocery nearby, the location of Helen's Beach House could not be more ideal. The exterior maintains a modest aesthetic, but this only serves as a cover of sorts for how... View all property information
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From
$650
Per Night
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1 / 21
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6 Bedrooms, 3 Bathrooms, Sleeps 10
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Amenities & Details
  • Garage
  • Microwave
  • Dishwasher
  • Washer
  • Dryer
  • Ceiling Fans
  • Parking
  • TV
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • Smoking allowed
  • Elder access
  • x
About this property
This home & location is a beach lovers paradise. Ideally set within a few steps to Kalama Beach park & world famous Kailua Beach. Fantastic family home with back yard that doesnt end. Newly refinished pool & deck with an extra 6th bedroom (cabana) for more privacy. Gorgeous solarium for... View all property information
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From
$395
Per Night
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1 / 21
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4 Bedrooms, 3 Bathrooms, Sleeps 8
Bookings
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Amenities & Details
  • Microwave
  • Dryer
  • Stove
  • TV
  • Grill
  • DVD Player
  • Washer
  • Refrigerator
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
Hale Maluhia (House of Serenity) is a kama'aiana style home near Kailua Beach. In a quiet Kailua neighborhood, the home is a quick 5 minute, one block walk to the world famous secluded white sand beach. Relax with friends and family in this child-friendly family home. Experience the warm 'old... View all property information
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From
$330
Per Night
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1 / 14
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3 Bedrooms, 2 Bathrooms, Sleeps 8
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Amenities & Details
  • Parking
  • Air Conditioning
  • Stove
  • Washer
  • Grill
  • TV
  • Microwave
  • Ceiling Fans
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
Makana's Place is a three bedroom, two bath home in quaint Kailua Town. This Non-Smoking home is very spacious over 1600 square feet living quarters, which is equivalent to a 4-5 bedroom home. Beautifully decorated with well quality furniture (Koa). Makana's Place features a full kitchen plus... View all property information
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From
$450
Per Night
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1 / 10
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3 Bedrooms, 2 Bathrooms, Sleeps 6
Bookings
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Amenities & Details
  • Stove
  • Ceiling Fans
  • Refrigerator
  • Internet Access
  • Grill
  • Dryer
  • Washer
  • Microwave
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
Within half an hour of Honolulu International Airport and Waikiki, this quaint beach house sits on one of the most beautiful beaches in the state of Hawaii - Kailua- miles of white sand, with water sports, dining, sunrise and sunset beach walks, and private hot tub. It is an easy drive to Sea Life... View all property information
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From
$345
Per Night
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1 / 10
2 Bedrooms, 1 Bathroom, Sleeps 4
Details Reviews (7) Make Inquiry
Amenities & Details
  • Grill
  • Ceiling Fans
  • Number Of Bedrooms
  • # Of Bathrooms
  • Guest Count
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
You will find Serenity here. This is the beachfront cottage you've been searching for.This delightful cottage is found in the middle of stunning Kailua Beach. Casually lounge in the small but cozy living room and be astounded by breathtaking views of the beach. Step out your front door and onto... View all property information
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4 of 5 stars Reviewed August 21, 2013
Our family (children age 11 and 9) stayed here for our summer vacation. The location is about as perfect as you can get. A short walk across the lawn right onto one of the most...
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From
$550
Per Night
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1 / 32
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3 Bedrooms, 3 Bathrooms, Sleeps 8
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Amenities & Details
  • DVD Player
  • Washer
  • Refrigerator
  • Stove
  • Garage
  • TV
  • Grill
  • Microwave
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
Endless Summer Getaway.... the name says it all. This fabulous upgraded three bedroom three bath home boasts pride of ownership along with a feeling of hospitality. As you enter into the home you walk into the living/family room, then straight ahead is the sliding door that leads to the outdoor... View all property information
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From
$139
Per Night
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1 / 8
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Studio, 1 Bathroom, Sleeps 3
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Amenities & Details
  • # Of Bathrooms
  • Guest Count
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
Sleep till noon. You'll like the Beach Bungalow at Kailua Guesthouse. This large studio cottage has a California king bed and a queen-size sofa bed. There's a large lanai with park bench and bistro table. Full bath with tub and shower. Complimentary assigned parking on property and laundry... View all property information
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From
$350
Per Night
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1 / 13
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2 Bedrooms, 2 Bathrooms, Sleeps 4
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Amenities & Details
  • Refrigerator
  • Stove
  • Patio
  • Microwave
  • Satellite TV
  • Parking
  • TV
  • Ceiling Fans
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
This cute quaint cottage is perfect for a vacation! It feels of beach house when you walk into it. With in walking distance to many beach access points along Lanikai beach. Luxury views and surroundings at your fingertips. This very new rental has been renovated and re-decorated for a clean,... View all property information
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From
$875
Per Night
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1 / 6
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3 Bedrooms, 3 Bathrooms, Sleeps 6
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Amenities & Details
  • Refrigerator
  • Parking
  • Washer
  • TV
  • Stove
  • Grill
  • Patio
  • DVD Player
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • Smoking allowed
  • Elder access
  • x
About this property
Old Hawaiiana steps from the world-famous, Lanikai Beach, this three bedroom, three bath retreat has the true feel of the Hawaii of yester-year. Hale Maluhia is tropically decorated with all amenities for your comfort. Art work has been hand selected from local artists. Marble and Travertine... View all property information
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From
$1,050
Per Night
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1 / 31
6 Bedrooms, 5 Bathrooms, Sleeps 12
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Amenities & Details
  • Guest Count
  • # Of Bathrooms
  • Grill
  • Parking
  • TV
  • Waterfront
  • Linens Provided
  • Number Of Bedrooms
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Seaside is a classic beachfront estate reminiscent of 'Old Hawaii'. Coconut trees abound throughout the spacious lush green lawns. WIth large open spaces, both inside and out, this home is perfect for big families or family reunions. Seaside sits on Kailua Beach, one of the most beautiful beaches... View all property information
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5 of 5 stars Reviewed August 16, 2014
The pictures do not provide justice to the true beauty and convenience of the yard and beach. It is spectacular! The house is large and comfortable . It worked well for my...
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From
$550
Per Night
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1 / 27
Payment Protection
4 Bedrooms, 3 Bathrooms, Sleeps 8
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Amenities & Details
  • DVD Player
  • Grill
  • TV
  • Parking
  • Garage
  • Dishwasher
  • Washer
  • Fireplace
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
This Custom beachside home is steps from beautiful Kailua beach. It features a refreshing cobalt blue pool and spa, as well as, a gas firepit for those evenings by the pool. As it's a custom home it offers an indoor fire place and vaulted ceilings, wood floors, berber carpet and the original art... View all property information
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From
$475
Per Night
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1 / 21
Payment Protection
3 Bedrooms, 3 Bathrooms, Sleeps 8
Booking
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Amenities & Details
  • Dishwasher
  • Stove
  • Microwave
  • Parking
  • Patio
  • Washer
  • Ceiling Fans
  • Satellite TV
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
Our Hawaiian-style 3 bedroom 3 bath vacation home is just steps from the sand of beautiful Kailua Beach on the island of Oahu. Hear the sounds of the surf at night and the trade winds through the coconut trees. Relax. Walk on the beach. Swim. Lay in the sun. Enjoy life Hawaiian-style. Our home is... View all property information
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From
$900
Per Night
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1 / 2
Payment Protection
5 Bedrooms, 3 Bathrooms, Sleeps 10
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Amenities & Details
  • Grill
  • Refrigerator
  • Microwave
  • Hot Tub
  • Parking
  • Safe
  • TV
  • Garage
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • Smoking allowed
  • Elder access
  • x
About this property
Breath-taking views . . . luxurious details . . . This is Shangri-La by the Sea. Leave your worries behind as you step into this magical home. Nourish your soul as the waves break just outside your door. Rejuvenate your mind, and cherish friends and family as you settle into this luxurious,... View all property information
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From
$195
Per Night
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1 / 15
Payment Protection
1 Bedroom, 1 Bathroom, Sleeps 3
Bookings
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Amenities & Details
  • Deck
  • Grill
  • TV
  • DVD Player
  • Refrigerator
  • Dryer
  • Washer
  • Stove
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • Smoking allowed
  • Elder access
  • x
About this property
Welcome. This is it! This is the one you've been looking for. Enjoy sleeping on a comfortable King Size Bed. Convenient location in Kailua, clean and breezy, Air conditioned, Wi-Fi, and Ceiling Fans. Fully-Equipped Kitchen includes, microwave, toaster, coffee maker, 4-burner stove with oven, rice... View all property information
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From
$995
Per Night
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1 / 38
4 Bedrooms, 4 Bathrooms, Sleeps 9
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Amenities & Details
  • Parking
  • Patio
  • Garage
  • Grill
  • Refrigerator
  • TV
  • Hot Tub
  • Microwave
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Kapoho Hale, situated on Kapoho Cape in the Kaimalino neighborhood of Kailua, Oahu was newly constructed in 2007 and remains in immaculate condition. This amazing home has views of the entire east side of the island- from Makapuu Lighthouse to Kaaawa! Check out our YouTube video at:... View all property information
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From
$450
Per Night
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1 / 31
Payment Protection
3 Bedrooms, 3 Bathrooms, Sleeps 6
Booking
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Amenities & Details
  • Stove
  • TV
  • Fireplace
  • Parking
  • Grill
  • Washer
  • Refrigerator
  • Microwave
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
Hawaiian Paradise, across the street is a short path to Kailua Beach, voted #1 beach in America by Conde Nast Traveler Magazine. A beautiful rather secluded beach far less crowed than most beaches in Hawaii. This private home is a home away from home. This 3 bedroom, 3 Bath property is completely... View all property information
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From
$5,600
Per Week
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1 / 18
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8 Bedrooms, 4 Bathrooms, Sleeps 18
Details Reviews (3) Make Inquiry
Amenities & Details
  • Garage
  • TV
  • Stove
  • Dishwasher
  • Grill
  • Microwave
  • Refrigerator
  • Patio
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
The property is located approx. 10 miles from the city of Honolulu . 15 minutes walk to the nearest beach access. East of the island of Oahu . Surrounded by lush green mountains . The house has tranquil and peaceful atmosphere . This house is fully furnished in an authentic island style. The... View all property information
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4 of 5 stars Reviewed February 19, 2014
On our arrival we were met by Sonya (owner) with cup cakes for the boys. She welcomed us and gave us a tour of her house. House was clean, well decorated, and most of all...
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From
$199
Per Night
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1 / 20
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1 Bedroom, 1 Bathroom, Sleeps 3
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Amenities & Details
  • Washer
  • Stove
  • DVD Player
  • Safe
  • Ceiling Fans
  • Satellite TV
  • Microwave
  • Dryer
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • x
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
LOCATION, LUXURY, PRIVACY, & SECURITY. KAILUA DREAMS-PALI is the PERFECT Vacation Rental for the discerning and well travelled guests. Guests will appreciate the location, luxury, privacy, and security our unit offers. We are conveniently located in a quiet neighborhood halfway between the world... View all property information
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5 of 5 stars Reviewed December 18, 2014
This is a rental apartment with the owners living on property. It is nestled into the quiet, private, safe and non-tourist town of Kailua on the western shore. Sure beats paying...
5 of 5 stars Reviewed August 28, 2014
We enjoyed our time in Kailua. The apartment was perfect. We had a lot of space and everything was very clean.
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From
$199
Per Night
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1 / 22
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1 Bedroom, 1 Bathroom, Sleeps 2
Bookings
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Amenities & Details
  • Grill
  • Washer
  • Stove
  • Safe
  • Dishwasher
  • Dryer
  • Patio
  • Microwave
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • x
  • Smoking allowed
  • Elder access
  • x
About this property
LOCATION, LUXURY, PRIVACY, & SECURITY. KAILUA DREAMS-MAKAI is the PERFECT Vacation Rental for the discerning and well travelled guests. Guests will appreciate the location, luxury, privacy, and security our unit offers. We are conveniently located in a quiet neighborhood halfway between the... View all property information
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5 of 5 stars Reviewed February 8, 2015
Between my husband and I, we have been to many different places throughout the world and this by far was the best vacation EVER....and a huge part of it was due to this incredible...
4 of 5 stars Reviewed January 15, 2015
This was the first time we had hired a rental property in a another country using trip advisor and it was a pleasant experience. Cheryl (the owner) was very prompt in replying to...
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From
$650
Per Night
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1 / 19
6 Bedrooms, 3 Bathrooms, Sleeps 12
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Amenities & Details
  • DVD Player
  • TV
  • Number Of Bedrooms
  • Guest Count
  • Internet Access
  • Grill
  • # Of Bathrooms
  • Satellite TV
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
This home & location is a beach lovers paradise. Ideally set within a few steps to Kalama Beach park & world famous Kailua Beach. Fantastic family home with back yard that doesn’t end. Newly refinished pool & deck with an extra 6th bedroom (cabana) for more privacy. Gorgeous solarium for breakfast... View all property information
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From
$225
Per Night
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1 / 12
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2 Bedrooms, 2 Bathrooms, Sleeps 6
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Amenities & Details
  • Nearest Beach: 0.0...
  • Number Of Bedrooms
  • HNL: 19.9 mi
  • Living Room Seats...
  • Dining Seats (8)
  • Air Conditioning
  • Guest Count
  • # Of Bathrooms
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Beautiful Single Family Home is sought after neighborhood in Kailua. 15 minutes walk to the beach, Fully furnished with dishes, linens, kitchenware - everything you need. Accommodates 4-6 Some standout features are -- -- 2270 sq feet of house plus a yard that is about 1800 sq feet. -- beautiful... View all property information
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From
$199
Per Night
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1 / 23
Payment Protection
1 Bedroom, 1 Bathroom, Sleeps 3
Booking
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Amenities & Details
  • Stove
  • Wi-Fi
  • Internet Access
  • Ceiling Fans
  • Dryer
  • Microwave
  • Mountain Views
  • TV
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • x
About this property
Completely Renovated Cottage in Kailua in very close walking distance to the beach. High Speed Internet with WiFi Access, HD-TV, Oven, Microwave, Toaster, Coffee Maker, Refrigerator, Washer, Dryer, Bathtub. Eastern King Size Bed and additional sleeper couch for another Queen-Size Bed. Our Cottage... View all property information
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From
$360
Per Night
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1 / 13
Payment Protection
2 Bedrooms, 2 Bathrooms, Sleeps 4
Booking
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Amenities & Details
  • Patio
  • Satellite TV
  • DVD Player
  • Air Conditioning
  • Stove
  • Dryer
  • TV
  • Microwave
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • ?
  • ?
About this property
Beautiful 2 bedroom & 2 bathroom guest house, with private entrance, in a tropical and quiet setting. Lovely saltwater swimming pool with waterfall and relaxing surroundings. Private barbecue area, outdoor dining, also a luxury kitchen inside. Within walking distance to white sand Kailua Beach,... View all property information
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From
$139
Per Night
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1 / 7
Payment Protection
Studio, 1 Bathroom, Sleeps 2
Bookings
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Amenities & Details
  • Internet Access
  • Ceiling Fans
  • Microwave
  • TV
  • Hairdryer
  • Wi-Fi
  • Air Conditioning
  • Grill
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
Walk to Kailua Beach or Town. Located at: 131 Kuulei Road Kailua, Hawaii The Hawaii Sheffield House Ginger Studio is located between Kailua Beach and Kailua Town.The Hawaii Sheffield House has its own 'secret garden with an outdoor dining table. It is a delightful home away from home for... View all property information
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4 of 5 stars Reviewed January 31, 2014
We were surprised just how spacious this studio is and how nice and fresh it is. Lots of storage and it's well equipped. There were a plate of muffins waiting for us as well as...
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From
$500
Per Night
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1 / 30
Payment Protection
3 Bedrooms, 2 Bathrooms, Sleeps 8
Details Reviews (4) Make Inquiry
Amenities & Details
  • Dryer
  • TV
  • Washer
  • Grill
  • Dishwasher
  • Safe
  • Patio
  • Refrigerator
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
Aloha and welcome to your beach house. This charming home has everything you need for your dream vacation. Bring your family and friends to unwind Island-style. Come on in and make yourself comfortable. As soon as you walk through the door the stress of everyday life will melt away. Most of the... View all property information
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5 of 5 stars Reviewed February 23, 2015
This was our first trip to Oahu, and we loved being on the quiet side of the island! What a wonderful home! We hit Costco on the way out from the airport and bouight groceries...
5 of 5 stars Reviewed November 18, 2014
This was our first visit to Hawaii and we loved every minute of it. The vacation home and owners were wonderful. The house was as described and perfect for our stay. The owners...
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From
$149
Per Night
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1 / 12
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Studio, 1 Bathroom, Sleeps 5
Bookings
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Amenities & Details
  • Grill
  • Ceiling Fans
  • Stereo System
  • DVD Player
  • Porch
  • Safe
  • Patio
  • Microwave
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
Spacious Studio with Private Entrance & Bathroom This beautiful studio is located in a quiet neighborhood close to world famous Kailua Beach. Property is on the water with a large swimming pool. The area is surrounded by lush tropical Gardens that offer many private seating areas for morning... View all property information
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From
$174
Per Night
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1 / 12
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1 Bedroom, 1 Bathroom, Sleeps 3
Bookings
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Amenities & Details
  • Parking
  • Grill
  • Air Conditioning
  • Ceiling Fans
  • Hairdryer
  • Refrigerator
  • Outdoor Dining Area
  • TV
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
Hawaii Sheffield House is located only 10 houses to Kailua Beach. The closest beach access is Kaapuni Loop. Sheffield House provides a home away from home for your Kailua Hawaii vacation. The Garden Suite has free off street parking, free extreme hi speed wifi, high definition cable TV,... View all property information
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From
$165
Per Night
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1 / 30
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Studio, 1 Bathroom, Sleeps 2
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Amenities & Details
  • Parking
  • Grill
  • TV
  • Stereo System
  • Dryer
  • Stove
  • Refrigerator
  • Washer
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
Footsteps to Hawaii's best beach and a short walk to town, shopping, restaurants, farmers markets and community center for tennis, pool and gym. Ideally located for many ocean sports, hiking and cycling to just about anywhere in this pedestrian and bike friendly beach town. The cottage is fully... View all property information
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5 of 5 stars Reviewed November 24, 2014
I highly recomend staying at one of Nancy's cottages in Kailua. The cottage I stayed in was immaculate and had every amenity you could wish for. The owners have created a true...
5 of 5 stars Reviewed October 19, 2014
Nancy's Cottage was recommended to us by friends - it was fabulous! My husband, 19yr old daughter and I went to visit our daughter and boyfriend's family. They only lived about...
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From
$175
Per Night
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1 / 18
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Studio, 1 Bathroom, Sleeps 4
Bookings
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Amenities & Details
  • Safe
  • Parking
  • Microwave
  • Stove
  • Patio
  • Washer
  • TV
  • Ceiling Fans
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
Footsteps to Hawaii's best beach. Newly constructed and fully furnished with all the amenity. It is a short walking distance to Kailua and Lanikai beaches, hiking, shopping, restaurants and fun. View all property information
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5 of 5 stars Reviewed September 22, 2014
We loved this wonderful spot. It was as described 5 minutes walk to the beach, beautifully presented, immaculately clean. Eveything we needed was there, they have really thought...
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From
$1,450
Per Night
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1 / 22
4 Bedrooms, 4 Bathrooms, Sleeps 8
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Amenities & Details
  • DVD Player
  • Air Conditioning
  • Terrace
  • TV
  • Parking
  • Grill
  • Ceiling Fans
  • Fireplace
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • ?
  • ?
About this property
This getaway’s name, Maluhia, translates into “Peace” in Hawaiian, and it’s not hard to see why—nestled in the region of Kailua, known for its turquoise waters, and white sandy beaches, you’ll feel relaxed in this tranquil space, it’s one of our top Oahu vacation rentals. The low-key area of Kailua... View all property information
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From
$1,800
Per Month
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1 / 10
Payment Protection
Studio, 1 Bathroom, Sleeps 2
Booking
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Amenities & Details
  • Parking
  • Wi-Fi
  • Ceiling Fans
  • TV
  • Patio
  • Washer
  • Grill
  • Microwave
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • Smoking allowed
  • Elder access
  • x
About this property
Enjoy peace and quiet in this quaint, private cottage with queen-size bed and kitchenette, lovely tropical yard with covered lanai, beach shower, and 1-1/2 blocks to famous Kailua beach. Walking/biking distance to boutiques and restaurants in Kailua town. There is a washer/dryer on premises and... View all property information
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5 of 5 stars Reviewed January 7, 2015
Happy we stayed here - Janet was friendly and easy to reach before and during our visit. Wonderful place for our staycation! Quiet neighborhood, comfy bed, clean accommodations...
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From
$185
Per Night
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1 / 24
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1 Bedroom, 1 Bathroom, Sleeps 2
Bookings
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Amenities & Details
  • Grill
  • Parking
  • Washer
  • Patio
  • Dryer
  • Refrigerator
  • Hot Tub
  • Microwave
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Stroll along the white sandy beaches of Lanikai Beach, named one of the top 10 beaches in the world by 2014 Travelers Choice on Trip Advisor! Only a 5 minute drive from our stunning one-bedroom. We are situated on a picturesque, family-friendly road with little road noise and traffic. Breathtaking... View all property information
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5 of 5 stars Reviewed November 9, 2014
My husband and I stayed at Lanikai Love for 10 days for our honeymoon. We absolutely loved every second of our stay here! The property is exactly as described and even more...
3 of 5 stars Reviewed September 20, 2014
Not pravite pool and hot tub, shared with others lived in that house. No late check out option 11:00 too early. Living room got only fan it's kind hot dining there.
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From
$130
Per Night
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1 / 18
Payment Protection
Studio, 1 Bathroom, Sleeps 2
Bookings
Details Make Inquiry
Amenities & Details
  • Hot Tub
  • TV
  • Washer
  • Patio
  • Dryer
  • Stove
  • Parking
  • Microwave
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Stroll along the white sandy beaches of Lanikai Beach, named one of the top 10 beaches in the world by 2014 Travelers Choice on Trip Advisor! Only a 5 minute drive from our stunning studio. We are situated on a picturesque, family-friendly road with little road noise and traffic. Breathtaking... View all property information
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From
$155
Per Night
View Details
1 / 21
Payment Protection
1 Bedroom, 1 Bathroom, Sleeps 2
Bookings
Details Make Inquiry
Amenities & Details
  • Dryer
  • Grill
  • Stove
  • Ceiling Fans
  • Microwave
  • Hot Tub
  • Patio
  • Refrigerator
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Stroll along the white sandy beaches of Lanikai Beach, named one of the top 10 beaches in the world by 2014 Travelers Choice on Trip Advisor! Only a 5 minute drive from our stunning one-bedroom. We are situated on a picturesque, family-friendly road with little road noise and traffic. Breathtaking... View all property information
Make Inquiry
From
$1,250
Per Night
View Details
1 / 24
4 Bedrooms, 4 Bathrooms, Sleeps 8
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Amenities & Details
  • Boat Available
  • Grill
  • Wi-Fi
  • Parking
  • # Of Bathrooms
  • Number Of Bedrooms
  • Guest Count
  • Linens Provided
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • ?
  • ?
About this property
Description Our BEACHFRONT home is designed to provide you with a perfect vacation retreat. The house is as close to the beach as you legally can build. The beach of Kailua is renown for its fine white sand, blue green waters and safety. This is not a crowded beach, but has a pleasant neighborhood... View all property information
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Kailua Vacation Rentals

Kailua's pristine beaches and strong trade winds make it an excellent destination for swimming, sailing, kite-flying, or just relaxing and enjoying the view. If you are planning a trip to Kailua for your next vacation, why not try renting your very own vacation home instead of staying at a hotel? There are cozy rental condos perfect for a romantic beach getaway, luxurious beachfront houses spacious enough for the whole family, and everything in between. With the amazing assortment of vacation rentals in Kailua, there is sure to be a perfect rental for any budget or need. Vacation rentals provide a truly one-of-a-kind experience when traveling to Kailua, with all the privacy and space of your own home away from home.

A Kailua Vacation

Kailua Beach Park is one of the major destinations in the area, and has the unique distinction of being two separate and very different beaches divided by a small area. Both Kailua and Lanikai beaches attract swimmers, surfers, and boaters alike due to their soft white sand, beautiful waters, and postcard views of the two islands in the distance. After you hit the beach, how about a shopping trip to Kailua Farmer's Market for some fresh food, or Mu'umu'u Heaven for some unique island wear? Barbie lovers rejoice; Kailua is home to the Hawaii Loves Barbie Dolls Museum, a private collection that is free to check out if you make an appointment in advance. No matter how you decide to spend your time in Kailua, at the end of the day staying at your very own vacation rental will make your trip even more special.

Family-Friendly Kailua

From flying kites at the beach to enjoying the Barbie Dolls museum, there is plenty to do in Kailua that children will love. With vacation rentals, it is easy to bring along the entire family without worrying about renting extra hotel rooms. Your rental condo, villa, or beachfront home will have enough space for everyone. For large groups, it is the more comfortable and economical choice, and children will feel more secure knowing they are staying in a place that feels like home.